Dimethyl trans-1,2-cyclopropanedicarboxylate → rac-tert-butyl N-((1R,2R)-2-aminocyclopropyl)carbamate

HRID 405941Notes

Reaction equation

HRID 405941 reaction equation
[C@@H]1(C(OC)=O)C[C@H]1C(OC)=O.Cl.[C:13]([O:17][C:18]([NH:20][C@@H:21]1[CH2:23][C@H:22]1[NH2:24])=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18]([NH:20][C@@H:21]1[CH2:23][C@H:22]1[NH2:24])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 6429599Dimethyl trans-1,2-cyclopropanedicarboxylateHCID 57364724rac-tert-butyl N-[(1R,2R)-2-aminocyclopropyl]carbamate hydrochloride

Product 1

HCID 33746924rac-tert-butyl N-((1R,2R)-2-aminocyclopropyl)carbamate

Procedure

Starting from dimethyl trans-1,2-cyclopropanedicarboxylate, trans-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride may be prepared and purified analogously to cis-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride (see 58.4). M.p: 200-202° C.

Workup

  1. custommay be prepared
  2. custompurified analogously to cis-N-tert-butyloxycarbonyl-1,2-cyclopropanediamin hydrochloride (see 58.4)

Sources & evidence

ORD record
ord-117921532e5f4fddb34ec38de3ed4b42
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

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